2-(Bromomethyl)tetrahydro-2H-pyran → 6-fluoro-5-methoxy-1'-{[5-(trifluoromethyl)furan-2-yl]methyl}spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one
Reaktionsgleichung
Br[CH2:2][C:3]1[O:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][CH:4]=1.BrCC1CCCCO1.[F:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][C:24]2[C:29]3([CH2:39][O:40][C:23]=2[CH:22]=1)[C:37]1[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=1)[NH:31][C:30]3=[O:38]>>[F:20][C:21]1[C:26]([O:27][CH3:28])=[CH:25][C:24]2[C:29]3([CH2:39][O:40][C:23]=2[CH:22]=1)[C:37]1[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=1)[N:31]([CH2:2][C:3]1[O:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][CH:4]=1)[C:30]3=[O:38]Komponenten
Edukt 3
Produkt 1
Versuchsvorschrift
Following the procedure as described in EXAMPLE 4 and making non-critical variations using 5-bromomethyl-2-(trifluoromethyl)furan to replace 2-(bromomethyl)tetrahydro-2H-pyran, and 6-fluoro-5-methoxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, 6-fluoro-5-methoxy-1′-{[5-(trifluoromethyl)furan-2-yl]methyl}spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (43%) as a colorless solid: mp 132-134° C.; 1H NMR (300 MHz, CDCl3) δ7.58 (d, J=9.4 Hz, 1H), 7.27 (dd, J=7.7, 7.7 Hz, 1H), 7.06-7.01 (m, 2H), 6.84 (d, J=7.9 Hz, 1H), 6.71-6.67 (m, 2H), 6.62 (d, J=12.1 Hz, 1H), 6.34 (d, J=3.4 Hz, 1H), 6.10 (d, J=3.4 Hz, 1H), 4.90 (d, J=16.3 Hz, 1H), 4.57 (d, J=12.8 Hz, 1H), 4.45 (d, J=12.7 Hz, 1H), 4.41 (d, J=16.2 Hz, 1H), 3.91 (s, 3H); MS (ES+) m/z 433.9 (M+1).
Quellen und Nachweise
- ORD-Eintrag
- ord-6397c7e291bb40108e3d727ba4b04e0a
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08263606B2
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